Methanol → HCID 59515739, compound

HRID 1161216Notes

Reaction equation

HRID 1161216 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)[C:9]2=[O:14])([O-])=O.CO>[Pd]>[C:23]([O:22][C:20]([N:18]1[CH2:19][CH:16]([CH2:15][N:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[CH:13][C:4]=3[NH2:1])[C:9]2=[O:14])[CH2:17]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515907HCID 59515907, compound

Product 1

HCID 59515739HCID 59515739, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a round bottom flask was combined tert-butyl 3-((5-nitro-1-oxoisoquinolin-2(1H)-yl)methyl)azetidine-1-carboxylate (0.56 g, 0.0015 mol), palladium on C (0.16 g, 0.0015 mol) and methanol (50 mL, 1 mol). The reaction mixture was stirred under hydrogen balloon at room temperature overnight. The mixture was filtered over celite, MeOH was removed and purified by silica-gel column twice (DCM:MeOH and EtOAc:Hexane). A white solid was obtained (190 mg). MS m/z=330.0 (M+1).

Workup

  1. customInto a round bottom flask was combined
  2. filtrationThe mixture was filtered over celite, MeOH
  3. customwas removed
  4. custompurified by silica-gel column twice (DCM:MeOH and EtOAc:Hexane)
  5. customA white solid was obtained (190 mg)

Sources & evidence

ORD record
ord-2a60f3ace22d428ca949da652b4e78c7
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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